Roasted Tomato Soup with Grilled Cheese

The smell of tomatoes roasting in the oven always makes me stop whatever I'm doing and just breathe it in. One chilly October afternoon, I tossed halved tomatoes onto a sheet pan without much of a plan, and by the time they'd caramelized, the whole kitchen smelled like a hug. I blended them into soup, then remembered the leftover sandwich bread and cheddar in the fridge. Those little grilled cheese cubes floating on top turned a simple bowl into something my kids still ask for by name.

I made this for my neighbor after she had surgery, and she called me later that evening just to say the croutons made her laugh out loud. She said it reminded her of being a kid, dunking grilled cheese into tomato soup on snow days. That's when I realized this recipe wasn't just about flavor, it was about comfort that feels like home even when you're far from it. Now I double the batch every time and keep extra croutons in a jar, because they disappear faster than I expect.

Ingredients

• Ripe tomatoes: Use the ripest tomatoes you can find, the kind that feel heavy and smell faintly sweet, because roasting concentrates everything including any blandness.
• Onion and garlic: Roasting them whole mellows their sharpness into a soft, almost caramelized sweetness that becomes the soup's backbone.
• Olive oil: A good drizzle helps the vegetables blister and brown instead of just steaming, and those browned bits are where the magic hides.
• Vegetable broth: Homemade is lovely, but a quality store bought version works perfectly and saves you an hour.
• Tomato paste: Just one tablespoon deepens the tomato flavor without making the soup taste heavy or canned.
• Heavy cream or milk: This is optional, but a splash makes the texture velvety and rounds out any lingering acidity.
• Sharp cheddar cheese: The sharper the better for the croutons, it holds up to the heat and gives you that satisfying cheese pull.
• Sandwich bread: Plain white or whole wheat both work, just make sure it's soft enough to crisp up without turning into hard toast.
• Butter: Softened butter spreads easily and crisps the bread into golden, crackling perfection.

Instructions

Roast the vegetables:

Preheat your oven to 400°F and arrange the tomato halves cut side up on a baking sheet alongside the onion quarters and garlic cloves. Drizzle everything with olive oil, season generously with salt, pepper, and thyme or basil, then roast for 25 to 30 minutes until the tomatoes are soft, jammy, and starting to char at the edges.

Simmer the soup base:

Transfer all the roasted vegetables and any sticky, caramelized juices from the pan into a large pot, then add the vegetable broth, tomato paste, and a teaspoon of sugar if your tomatoes are on the tart side. Let everything simmer gently over medium heat for about 10 minutes, stirring occasionally so the flavors can meld together.

Blend until silky:

Use an immersion blender right in the pot to puree the soup until it's completely smooth, or carefully transfer it in batches to a countertop blender. Stir in the cream or milk if you want that luxurious, velvety texture, then taste and adjust the seasoning with more salt or a pinch of sugar.

Make the grilled cheese croutons:

Butter one side of each bread slice, layer the cheese between two slices with the buttered sides facing out, then cook in a heated skillet over medium heat for 2 to 3 minutes per side until golden and the cheese is fully melted. Let the sandwiches cool just enough to handle, then cut them into bite sized cubes.

Serve and enjoy:

Ladle the hot soup into bowls and scatter a handful of grilled cheese croutons on top. Serve immediately while the croutons are still warm and crispy.

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My son once told me this soup tasted like a cozy blanket, which is maybe the highest compliment a seven year old can give. We were sitting at the table on a rainy Sunday, and he fished out every single crouton before he even touched the soup itself. I didn't mind, because watching him giggle at the melted cheese threads made me realize that some recipes are less about perfection and more about the moments they create.

Choosing Your Tomatoes

I've learned that in the summer, any heirloom or farmers market tomato will give you incredible flavor, but in the winter, regular plum or Roma tomatoes actually roast up beautifully because they have less water and more flesh. If your tomatoes look a little pale or feel firm, don't worry, the oven works magic on them. I once used a mix of cherry tomatoes and beefsteaks because that's all I had, and the soup turned out even better, a little sweeter and more layered. The key is really just making sure they're ripe enough to smell like tomatoes when you cut into them.

Blending Without the Mess

If you're using a countertop blender, let the soup cool for a few minutes first and never fill the blender more than halfway, because hot liquid expands and I've learned that lesson the hard way with a ceiling splattered in tomato. Hold a kitchen towel over the lid while you blend, and start on the lowest speed before ramping up. An immersion blender is honestly a game changer for this recipe, you can blend right in the pot and there's almost no cleanup. Either way, blend longer than you think you need to, a truly smooth soup makes all the difference in how it feels on your tongue.

Making It Your Own

This soup loves a little improvisation, so don't be afraid to play around with the flavors and textures based on what you have or what sounds good. I've stirred in a spoonful of pesto at the end for a basil kick, or topped it with crispy bacon bits when I wanted something a little heartier. A drizzle of balsamic vinegar just before serving adds a subtle tang that makes the tomatoes sing even louder.

• Try sprinkling smoked paprika into the roasting pan for a subtle, smoky depth that feels almost like a campfire.
• Swap the cheddar in the croutons for Gruyère or mozzarella if you want a milder, stretchier cheese pull.
• For a vegan version, use coconut cream instead of dairy, and there are some truly great plant based cheeses now that melt beautifully in a hot skillet.

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This soup has become my go to whenever I need something that feels like a warm hug in a bowl, and those little grilled cheese croutons never fail to make people smile. I hope it brings as much comfort to your table as it has to mine.

Recipe FAQ

→ Can I make the soup ahead of time?

Yes, the roasted tomato soup stores well. Prepare it up to 2 days in advance and refrigerate in an airtight container. Reheat gently over medium heat, stirring occasionally. The grilled cheese croutons are best made fresh for maximum crispiness, but you can prepare the soup components ahead and assemble when serving.

→ What type of tomatoes work best for roasting?

Use ripe, firm tomatoes like Roma, San Marzano, or heirloom varieties. Fresh, in-season tomatoes deliver the best flavor. If fresh tomatoes aren't available, high-quality canned tomatoes can substitute—just drain excess liquid before roasting or use about 1.5 lbs equivalent.

→ How do I get the croutons extra crispy?

Toast the bread lightly before assembling the grilled cheese sandwiches. Cook over medium heat rather than high heat to allow the cheese to melt completely while the exterior becomes golden and crispy. Cut into cubes immediately after cooling for the best texture, and serve within a few minutes of preparation.

→ Can I freeze this soup?

Absolutely. Cool the blended soup completely, then transfer to freezer-safe containers in portion sizes. It keeps for up to 3 months. Thaw overnight in the refrigerator and reheat gently on the stovetop. Add cream or milk after thawing for the best consistency. The croutons should not be frozen; prepare them fresh.

→ What are good cheese alternatives for the croutons?

Sharp cheddar provides the classic flavor, but Gruyère adds nuttiness, mozzarella offers mildness, or smoked gouda brings depth. For dairy-free versions, use quality vegan cheese alternatives. Avoid cheeses that don't melt well; opt for varieties specifically designed for melting and grilling.

→ How do I adjust the soup's consistency?

For a thicker soup, use less vegetable broth or blend longer. For a thinner consistency, add more broth, cream, or milk gradually until reaching desired texture. If using an immersion blender, blend more vigorously for creamier results or less for a chunkier texture.